Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine‡

文献信息

发布日期 2017-04-04

DOI 10.1039/C7QO00188F

影响因子 5.281

作者

Arno Schneeweis, Andreas Neidlinger, Guido J. Reiss, Walter Frank, Katja Heinze, Thomas J. J. Müller

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摘要

A p-tert-butylphenyl substituted 4H-dithieno[2,3-b:3′,2′-e][1,4]thiazine was synthesized by twofold Buchwald–Hartwig coupling. The electronic properties (UV/Vis, cyclic voltammetry and spectroelectrochemistry) and the DFT- and TD DFT-calculated electronic structure reveal that the parent system and the radical cation and dication oxidation products are highly polarizable π-systems with strong charge transfer contributions. The radical cation and the dication were prepared by oxidation with antimony(V) pentachloride, giving stable deeply colored salts. EPR spectroscopy of the radical cation furnishes hyperfine coupling constants with the nitrogen nucleus and the α-thienyl protons. The dication is EPR silent and was structurally characterized by recording an NMR spectrum.

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来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry